Trifluoroacetic acid → HCID 66778197, compound

HRID 2091138Notes

Reaction equation

HRID 2091138 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11](=O)[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+].C([BH3-])#N.[Na+].FC(F)(F)C(O)=O>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C.C(Cl)Cl.C(N(CC)CC)C>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:11]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1)[CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

11

Reactant 5

HCID 6422Trifluoroacetic acidHCID 12082Methyl 4-aminobenzoateHCID 516892Sodium Bicarbonate2×HCID 5003444Sodium cyanoborohydrideHCID 66779142HCID 66779142, compound

Product 1

HCID 66778197HCID 66778197, compoundYield 27%

Reagents, catalysts & solvents 5

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 1-(3-methyl-1-benzofuran-2-yl)-2-phenoxyethanone (697 mg) synthesized above, methyl 4-aminobenzoate (399 mg), triethylamine (2.93 mL) and methylene chloride (10 mL) was added titanium (IV) chloride (344 μL) at 0° C. under argon atmosphere, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, methylene chloride was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a dark brown oil. To a solution (20 mL) of the obtained oil in tetrahydrofuran were added acetic acid (2 mL) and sodium cyanoborohydride (329 mg), and the mixture was stirred at room temperature for 15 min. Trifluoroacetic acid (2 mL) was added to the reaction mixture, and the mixture was further stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (25% ethyl acetate/hexane) to give the title object compound (279 mg, 27%) as a yellow solid.

Workup

  1. customto quench
  2. customthe reaction, methylene chloride
  3. customwas evaporated in an evaporator
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a dark brown oil
  9. stirringthe mixture was stirred at room temperature for 15 min
  10. stirringthe mixture was further stirred at room temperature for 3 hr
  11. customto quench
  12. customthe reaction
  13. extractionthe reaction mixture was extracted with ethyl acetate
  14. washThe extract was washed with saturated brine
  15. dry with materialdried over magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c334f32e20054b06a772c3366446c31c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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